CA2199846A1 - Use of aryluracils in semi-selective and non-selective weed control - Google Patents
Use of aryluracils in semi-selective and non-selective weed controlInfo
- Publication number
- CA2199846A1 CA2199846A1 CA002199846A CA2199846A CA2199846A1 CA 2199846 A1 CA2199846 A1 CA 2199846A1 CA 002199846 A CA002199846 A CA 002199846A CA 2199846 A CA2199846 A CA 2199846A CA 2199846 A1 CA2199846 A1 CA 2199846A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally substituted
- alkoxy
- represents hydrogen
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention concerns the use of aryluracils and arylthiouracils of general formula (I) or of isomer compounds thereof of general formula (Ia), in which formulae Q1, Q2, R1, R2, R3, R4, R5 and R6 each have the meanings given in the description, and optionally of one or a plurality of compounds from a second group of herbicides in semi-selective and non-selective weed control.
Description
l' ~ Le A 30 670-PCT 0 2 1 9 9 8 4 6 ~ -~A~ `.T~
Use of a~ acils in the field of semi-selective and non scle~e weed cont~l The invention relates to the use of known aryluracils (or aryl-thiouracils - or of compounds which are isomeric to these aryluracils or aryl-thiouracils) for semi-selective and non-selective weed control.
5 Aryluracils (or aryl-thiouracils) are herbicides subject-matter of a series of patent applications (cf. WO-A 91/00278, US Patent Specification 4979982, US Patent Specification 5169430, EP-A 408382, EP-A 563384, US Patent Specification 5084084, US Patent Specification 5127935, US Patent Specification 5154755, German Patent Specification 4327743, German Patent Specification 4343451, German Patent Specification 4414326). However, nothing hæ been disclosed on the use of the known aryluracils (or aryl-(thio)uracils) in the semi-selective and non-selective field of weed control.
Surprisingly, it has now been found that a series of known herbicidally active compounds from the group of the aryluracils (or aryl-thiouracils - or compounds which 15 are isomeric to these aryluracils or aryl-thiouracils) are highly suitable for controlling monocotyledon and dicotyledon weeds in the semi-selective and non-selective fields -alone, but also when used together with known herbicidally active compounds, for example from the substance classes of the carboxylic acids, diphenyl ethers, diazin(on)es or triazin(on)es, ureas and pyridine derivatives.
20 The invention therefore relates to compositions for controlling weeds in the semi-selective and non-selective field, characterized in that they comprise an effective amount of an aryluracil, or an aryl-thiouracil, of the general formula (I) ~ ~fZ
R ~ \~ (I) or of a compound of the general formula (Ia) which is isomeric to the above R~ N~Q Rt N ~ (la) Q ~ R2 where, in formulae (I) and (Ia), in each case Q' represents oxygen or sulphur, Q2 represents oxygen or sulphur, 5 Rl represents hydrogen or halogen, R2 represents halogen or cyano, R3 represents the group below Al A2 A3 in which Le A 30 670 A' represents a single bond, or represents oxygen, sulphur, -SO-, -SO2-, -CO-or the group -N-A4- where A4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, or A' fi~rthermore represents in each case optionally substituted ~lk~nel1iyl, S ~lkene~liyl~ ~7~1kenediyl, alkinediyl, cyclo~lk~ne~liyl, cycloalkenediyl or arenediyl, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 rel)le3e~ hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulphonyl or arylsulphonyl, or A2 filrthermore represents in each case optionally ~liLul~d ~lk~ne~liyl, alkenediyl, ~7~1kene-1iyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and A3 represents hydrogen, hydroxyl, melcapll~, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alk(lxyc~ubonyl, dialkoxy(thio)phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylidene~mino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl, R4 represents hydrogen, halogen or optionally substituted alkyl, Le A 30 670 R5 represents hydrogen, halogen or optionally substituted alkyl, and R6 represents hydrogen, hydroxyl, amino, or in each case optionally substituted alkyl, alkoxy, alkenyl or alkinyl, and, if al~plopliate, one or more compounds from a second group of herbicides which S contains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-bl-t~n~te (glufosinate ammonium), ~-(hydroxymethylphosphinyl)- 1 -a-aminobutyryl- 1 -alanyl- 1 -alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) diazin(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino- 1,3 ,S -triazine (atrazine), 2-chloro-4,6-bis-ethylamino- 1,3 ,S -triazine (.sim~in), S-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin), (d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)- 1 -(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium Le A 30 670 chloride (paraquat) or l,1'-ethylene-2,2'-bipyridinium chloride (diquat).
Herbicidal compositions according to the invention which are of particular interest are those with a compound of the formula (I) or (Ia) - above - where Q~ replcs~ s oxygen or sulphur, 5 Q2 r~plc;stlll~ oxygen or sulphur, Rl represents hydrogen, fluorine, chlorine or bromine, R2 represents fluorine, chlorine, bromine, iodine or cyano, R3 represents the group below -Al A2 A3 in which Al represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 ~e~lesc;lll~i hydrogen, hydroxyl, C~-C4-alkyl, Cl-C4-alkoxy, phenyl, C,-C4-alkylsulphonyl or phenylsulphonyl, or Al furthermore represents C l -C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo~lkenerliyl or phenylene each of which is optionally substituted by fluorine, chlorine or bromine, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, Cl-C4-alkyl, C,-C4-alkoxy, Le A 30 670 phenyl, C,-C4-alkylsulphonyl or phenylsulphonyl, or A2 furthermore represents Cl-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo~lkene-liyl or phenylene each of which is optionally substituted S by fluorine, chlorine or bromine, A3 r~rese~ hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen or Cl-C4-alkoxy, or represents alkenyl, alkenyloxy, alkenylamino, alkylicl~nP~minQ, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and each of which is optionally substituted by halogen, or leplesellL~ compounds from cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkyli~l~ne~minc), cycloalkyloxycarbonyl or cycloalkylalkoxyc~LIbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if a~lo~liate 1 to 4 carbon atoms in the alkyl groups and each of which is optionally ~lb~LiLuLed by halogen, cyano, carboxyl, C~-C4-alkyl and/or Cl-C4-alkoxy-carbonyl, orrepresents phenyl, phenyloxy, phenyl-CI-C4-alkyl, phenyl-CI-C4-alkoxy, phenyloxycarbonyl or phenyl-CI-C4-alkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen C,-C4-alkyl, Cl-C4-halogenoalkyl, Cl-C4-alkyloxy, Cl-C4-halogenoalkyloxy and/or Cl-C4-alkoxy-carbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thi~ olyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-CI-C4-alkyl, furyl-CI-C4-alkyl, Le A 30 670 thienyl-C~-C4-alkyl, oxazolyl-CI-C4-alkyl, isoxazol-C~-C4-alkyl, thiazol-C,-C4-alkyl, pyridinyl-C,-C4-alkyl, pyrimidinyl-C,-C4-alkyl, pyrazolylmethoxy, furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy, 5 R4 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, R5 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, and R6 represents hydrogen, hydroxyl, amino, or le~reselll~ alkyl, alkoxy, alkenyl or alkinyl, each of which has up to 4 carbon atoms and each of which is optionally substituted by fluorine, chlorine or cyano, and, if applol,l;ate, with one or two further compounds from a second group of herbicides which contains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), l S 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-butanoate (glufosinate ammonium), r-(hydroxymethylphosphinyl)- 1 -a-aminobutyryl- 1 -alanyl- 1 -alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylarnmonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl-3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
Le A 30 670 (c) diazin(on)es, or triazin(on)es, such as, for exarnple, 2-chloro-4-ethylarnino-6-i-propyl-amino-1,3,5-kiazine(akazine),2-chloro-4,6-bis-ethylamino-1,3,5-kiazine (~im~7in), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-kiazin-5-one (mekibuzin);
5 (d) ureas such as, for e~mple, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)- 1 -(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or l,1'-ethylene-2,2'-bipyridinium chloride (diquat).
10 Herbicidal compositions according to the invention which are of very particular interest are those with a compound of the formula (I) or (Ia) - above - where Q' represents oxygen or sulphur, Q2 represents oxygen or sulphur, Rl represents hydrogen, fluorine, chlorine or bromine, 15 R2 represents fluorine, chlorine, bromine, iodine or cyano, R3 represents the group below -Al A2 A3 in which Al represents a single bond, or represents oxygen, sulphur, -SO-, -SO2-, -CO-Le A 30 670 or the group -N-A4- where A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl, or Al furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-S 1 ,1-diyl, propane-1,2-diyl, propane-1 ,3-diyl, ethene-1 ,2-diyl, propene-l ,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A2 represents a single bond or represents oxygen, sulphur, -SO-, -SO2-, -CO-or the group -N-A4-, where A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl, or A2 furthermore represents methylene, ethane-1, 1-diyl, ethane-1 ,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, or represents in each case fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-,i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethyl~l.lphinyl, n- ori-propyl~ulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, or represents propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, Le A 30 670 -lO- 02199846 butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, each of which is optionally substitued by fluorine or chlorine, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidçne~mint), cyclohexylidene~mino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxy-carbonyl or cyclohexylmethoxycalbollyl, each of which is optionally substituted by fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally fillly or partially hydrogenated) pyrrolyl, pyræolyl, imidazolyl, triazolyl, furyl, thienyl, oxæolyl, isoxazolyl, thiazolyl, isothiæolyl, o~r~ 701yl, thi~ olyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R4 represents hydrogen, fluorine, chlorine, or it represents methyl or ethyl, each of which is optionally substituted by fluorine and/or chlorine, R5 represents hydrogen, fluorine, chlorine, or it represents methyl or ethyl, each of which is optionally substituted by fluorine and/or chlorine, and Le A 30 670 1l02199846 R6 represents hydrogen, hydroxyl, amino, or represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, propenyl or propinyl, each of which is optionally substituted by fluorine, chlorine or cyano, and, if ~lopliate, with one or two compounds from a second group of herbicides 5 which contains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-bllt~n- ~te (glufosinate ammonium), ~-(hydroxymethylphosphinyl)- 1 -a-aminobutyryl- 1 -alanyl- 1 -alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) dia_in(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino- 1,3 ,S-tria_ine (atrazine), 2-chloro-4,6-bis-ethylamino- 1,3 ,5-triazine (~im~7in), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);
(d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)-1-(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or l,l'-ethylene-2,2'-bipyridinium chloride (diquat).
Le A 30 670 The following may be mentioned individually as examples of the compounds of the formula (I) to be used as components in mixtures, according to the invention:
1 -(4-chloro-3-methylsuphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-3-methylsulphonylamino-phenyl)-3 ,6-S dihydro-2,6-dioxo-3-amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-3-methylsulphonylaminophenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-3-ethylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-3-ethylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-3-ethylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-3-n-propylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimi~line, 1-(4-chloro-3-n-propylsulphonylamino-phenyl)-3, 6-dihydro-2 ,6-dioxo-3 -amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-3 -n-propylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl-1(2H)-pyrimi-lin~, 1-(4-chloro-3-i-propylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-3-i-propylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -amino-4-trifluoromethyl-1(2H)-pyrimidine, 1-(4-cyano-3-i-propylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-methylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-5-methylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-5 -methylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoro-methyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5 -ethylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2 ,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-ethylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl-1(2H)-pyrimidine~-(4-cyano-S-ethylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-n-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-5-n-propylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-amino-Le A 30 670 ~21 99 846 4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-5-n-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-5-i-propylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-i-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-cyano-5 -i-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-5-n-butylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine.
The compounds of the formula (I) - or (Ia) - are described in the Patent Applications and Patent Specifications given above.
Surprisingly, it has now been found that the above-defined active compounds of the formula (I) - or (Ia) - are particularly effective in the control of weeds in the semi-selective and non-selective field, if a~ropliate in combination with the active compounds mentioned above in the second group.
The active compounds, or active compound mixtures, to be used according to the invention can be employed not only in conventional cultivation methods (row crops with suitable distances between rows) in plantation crops (for example grape vines, fruit, citrus) and on industrial terrain and rail tracks, on paths and open areas, but also for stubble tre~tment and for the ~ -tillage method. They are furthermore suitable as desiccants (haulm killing for example in potatoes) or as defoliants (for example in cotton). They are are furthermore suitable for use on fallow land. Other fields of application are nurseries, forests, grassland and in the cultivation of on ~ment~
The following may be mentioned as examples of weeds which can be controlled wellby the active compounds, or active compound combinations, according to the invention:
Le A 30 670 Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, ~nth~mi~, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesb~ni~, Ambrosia, Solanum, Cirsium, Carduus, Sonchus, Rorippa, Rotala, T intl~rni~ Lamium, Veronica, Abutilon, Emex, Sida, Datura, 5 Viola, Galeopsis, Papaver, Cellldul~a, Trifolium, P~mmçlllus, Taraxum and Mentha.
Monocotyledon weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Bra~.hi~ri~ Lolium, Bromus, Avena, Cyperus, Sorhum, A~lol~yloll, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus,Papalum, T~çh~f nnum, Sphenoclea, Dactylocenium, Agrostis, Alopecurus and Apera;
10 However, the use of the active compounds and active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
If mixtures of the compounds of the formula (I) or (Ia) with the herbicides mentioned above under (a) to (e) ("second herbicide group") are used according to the invention, 15 the weight ratios of the active compounds in the active compound combinations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight,preferably 0.01 to 100 parts by weight, particularly preferably 0.1 to 10 parts by weight, of one or two of the herbicides mentioned above under (a) to (e) are generally used per part by weight of active compound of the formula (I) or (Ia).
20 The active compounds can be converted into the cll~tom~ry formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion conc~,ll,dl~s, natural and synthetic materials impregn~te~ with active compound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active 25 compounds with e~ten~lers, that is liquid solvents and/or solid carriers, optionally with Le A 30 670 the use of snrf~ct~nt~, that is emulsifiers and/or dispersants and/or foam-formers.
If water is used as an e~t~nller~ organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkyln~rhth~lenes, chlorinated aromatics and chlorinated aliphatic 5 hydrocarbons such as chloroben7~nes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl 10 sulphoxide, and water.
Suitable solid carriers are for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina andsilicates; suitable solid carriers for granules are: for example crushed and fractionated 15 natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic m~tPri~l such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emlll.cifiers andlor foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example 20 alkylaryl polyglycol ethers, alkylsulphonates, alkyl slllph~tes, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes such as gum arabic, polyvinyl alcohol and 25 polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
Le A 30 670 It is possible to use colorants such as inorganic pigment~, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, m~ng~nese, boron, copper, cobalt, molybdenum and zinc.
S The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The novel combinations of active compound are generally deployed as ready-to-useformulations. The active compounds present in the combinations may, however, also be mixed in individual forrnulations on use, i.e. deployed as tank mixes.
10 The active compounds and active compound combinations according to the invention, as such or in their formulations, can furthermore also be used for weed control in the form of a nlix~ with other known herbicides; again, readymixes or tank mixes arepossible. A mixture with other known active compounds such as fungicides, insecticides, acarizides, nematicides, bird repellants, growth substances, plant nutrients 15 and soil conditioners are also possible. For specific purposes, it may furtherrnore be advantageous to incorporate, in the formulations, vegetation-acceptable mineral or vegetable oils (for example "Oleo Dupont 1 lE", which is commercially available) or ammonium salts such as, for example, ammonium slllph~te or ammonium thiocyanate as further additives.
20 The active compounds or active compound combinations according to the invention can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or spreading.
25 In the use experiments which have been carried out, very good properties for use in the Le A 30 670 semi-selective and non-selective field of weed control was shown by the compounds of the formula (I) or (Ia) - also in combination with the herbicides from the second group, which are mentioned above under (a) to (e), such as, for example, the isopropyl ammonium salts of N-phosphonomethyl-glycine ("Roundup").
Le A 30 670
Use of a~ acils in the field of semi-selective and non scle~e weed cont~l The invention relates to the use of known aryluracils (or aryl-thiouracils - or of compounds which are isomeric to these aryluracils or aryl-thiouracils) for semi-selective and non-selective weed control.
5 Aryluracils (or aryl-thiouracils) are herbicides subject-matter of a series of patent applications (cf. WO-A 91/00278, US Patent Specification 4979982, US Patent Specification 5169430, EP-A 408382, EP-A 563384, US Patent Specification 5084084, US Patent Specification 5127935, US Patent Specification 5154755, German Patent Specification 4327743, German Patent Specification 4343451, German Patent Specification 4414326). However, nothing hæ been disclosed on the use of the known aryluracils (or aryl-(thio)uracils) in the semi-selective and non-selective field of weed control.
Surprisingly, it has now been found that a series of known herbicidally active compounds from the group of the aryluracils (or aryl-thiouracils - or compounds which 15 are isomeric to these aryluracils or aryl-thiouracils) are highly suitable for controlling monocotyledon and dicotyledon weeds in the semi-selective and non-selective fields -alone, but also when used together with known herbicidally active compounds, for example from the substance classes of the carboxylic acids, diphenyl ethers, diazin(on)es or triazin(on)es, ureas and pyridine derivatives.
20 The invention therefore relates to compositions for controlling weeds in the semi-selective and non-selective field, characterized in that they comprise an effective amount of an aryluracil, or an aryl-thiouracil, of the general formula (I) ~ ~fZ
R ~ \~ (I) or of a compound of the general formula (Ia) which is isomeric to the above R~ N~Q Rt N ~ (la) Q ~ R2 where, in formulae (I) and (Ia), in each case Q' represents oxygen or sulphur, Q2 represents oxygen or sulphur, 5 Rl represents hydrogen or halogen, R2 represents halogen or cyano, R3 represents the group below Al A2 A3 in which Le A 30 670 A' represents a single bond, or represents oxygen, sulphur, -SO-, -SO2-, -CO-or the group -N-A4- where A4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, or A' fi~rthermore represents in each case optionally substituted ~lk~nel1iyl, S ~lkene~liyl~ ~7~1kenediyl, alkinediyl, cyclo~lk~ne~liyl, cycloalkenediyl or arenediyl, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 rel)le3e~ hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulphonyl or arylsulphonyl, or A2 filrthermore represents in each case optionally ~liLul~d ~lk~ne~liyl, alkenediyl, ~7~1kene-1iyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and A3 represents hydrogen, hydroxyl, melcapll~, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alk(lxyc~ubonyl, dialkoxy(thio)phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylidene~mino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl, R4 represents hydrogen, halogen or optionally substituted alkyl, Le A 30 670 R5 represents hydrogen, halogen or optionally substituted alkyl, and R6 represents hydrogen, hydroxyl, amino, or in each case optionally substituted alkyl, alkoxy, alkenyl or alkinyl, and, if al~plopliate, one or more compounds from a second group of herbicides which S contains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-bl-t~n~te (glufosinate ammonium), ~-(hydroxymethylphosphinyl)- 1 -a-aminobutyryl- 1 -alanyl- 1 -alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) diazin(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino- 1,3 ,S -triazine (atrazine), 2-chloro-4,6-bis-ethylamino- 1,3 ,S -triazine (.sim~in), S-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin), (d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)- 1 -(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium Le A 30 670 chloride (paraquat) or l,1'-ethylene-2,2'-bipyridinium chloride (diquat).
Herbicidal compositions according to the invention which are of particular interest are those with a compound of the formula (I) or (Ia) - above - where Q~ replcs~ s oxygen or sulphur, 5 Q2 r~plc;stlll~ oxygen or sulphur, Rl represents hydrogen, fluorine, chlorine or bromine, R2 represents fluorine, chlorine, bromine, iodine or cyano, R3 represents the group below -Al A2 A3 in which Al represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 ~e~lesc;lll~i hydrogen, hydroxyl, C~-C4-alkyl, Cl-C4-alkoxy, phenyl, C,-C4-alkylsulphonyl or phenylsulphonyl, or Al furthermore represents C l -C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo~lkenerliyl or phenylene each of which is optionally substituted by fluorine, chlorine or bromine, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, Cl-C4-alkyl, C,-C4-alkoxy, Le A 30 670 phenyl, C,-C4-alkylsulphonyl or phenylsulphonyl, or A2 furthermore represents Cl-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo~lkene-liyl or phenylene each of which is optionally substituted S by fluorine, chlorine or bromine, A3 r~rese~ hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen or Cl-C4-alkoxy, or represents alkenyl, alkenyloxy, alkenylamino, alkylicl~nP~minQ, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and each of which is optionally substituted by halogen, or leplesellL~ compounds from cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkyli~l~ne~minc), cycloalkyloxycarbonyl or cycloalkylalkoxyc~LIbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if a~lo~liate 1 to 4 carbon atoms in the alkyl groups and each of which is optionally ~lb~LiLuLed by halogen, cyano, carboxyl, C~-C4-alkyl and/or Cl-C4-alkoxy-carbonyl, orrepresents phenyl, phenyloxy, phenyl-CI-C4-alkyl, phenyl-CI-C4-alkoxy, phenyloxycarbonyl or phenyl-CI-C4-alkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen C,-C4-alkyl, Cl-C4-halogenoalkyl, Cl-C4-alkyloxy, Cl-C4-halogenoalkyloxy and/or Cl-C4-alkoxy-carbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thi~ olyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-CI-C4-alkyl, furyl-CI-C4-alkyl, Le A 30 670 thienyl-C~-C4-alkyl, oxazolyl-CI-C4-alkyl, isoxazol-C~-C4-alkyl, thiazol-C,-C4-alkyl, pyridinyl-C,-C4-alkyl, pyrimidinyl-C,-C4-alkyl, pyrazolylmethoxy, furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy, 5 R4 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, R5 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, and R6 represents hydrogen, hydroxyl, amino, or le~reselll~ alkyl, alkoxy, alkenyl or alkinyl, each of which has up to 4 carbon atoms and each of which is optionally substituted by fluorine, chlorine or cyano, and, if applol,l;ate, with one or two further compounds from a second group of herbicides which contains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), l S 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-butanoate (glufosinate ammonium), r-(hydroxymethylphosphinyl)- 1 -a-aminobutyryl- 1 -alanyl- 1 -alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylarnmonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl-3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
Le A 30 670 (c) diazin(on)es, or triazin(on)es, such as, for exarnple, 2-chloro-4-ethylarnino-6-i-propyl-amino-1,3,5-kiazine(akazine),2-chloro-4,6-bis-ethylamino-1,3,5-kiazine (~im~7in), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-kiazin-5-one (mekibuzin);
5 (d) ureas such as, for e~mple, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)- 1 -(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or l,1'-ethylene-2,2'-bipyridinium chloride (diquat).
10 Herbicidal compositions according to the invention which are of very particular interest are those with a compound of the formula (I) or (Ia) - above - where Q' represents oxygen or sulphur, Q2 represents oxygen or sulphur, Rl represents hydrogen, fluorine, chlorine or bromine, 15 R2 represents fluorine, chlorine, bromine, iodine or cyano, R3 represents the group below -Al A2 A3 in which Al represents a single bond, or represents oxygen, sulphur, -SO-, -SO2-, -CO-Le A 30 670 or the group -N-A4- where A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl, or Al furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-S 1 ,1-diyl, propane-1,2-diyl, propane-1 ,3-diyl, ethene-1 ,2-diyl, propene-l ,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A2 represents a single bond or represents oxygen, sulphur, -SO-, -SO2-, -CO-or the group -N-A4-, where A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl, or A2 furthermore represents methylene, ethane-1, 1-diyl, ethane-1 ,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, or represents in each case fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-,i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethyl~l.lphinyl, n- ori-propyl~ulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, or represents propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, Le A 30 670 -lO- 02199846 butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, each of which is optionally substitued by fluorine or chlorine, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidçne~mint), cyclohexylidene~mino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxy-carbonyl or cyclohexylmethoxycalbollyl, each of which is optionally substituted by fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally fillly or partially hydrogenated) pyrrolyl, pyræolyl, imidazolyl, triazolyl, furyl, thienyl, oxæolyl, isoxazolyl, thiazolyl, isothiæolyl, o~r~ 701yl, thi~ olyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R4 represents hydrogen, fluorine, chlorine, or it represents methyl or ethyl, each of which is optionally substituted by fluorine and/or chlorine, R5 represents hydrogen, fluorine, chlorine, or it represents methyl or ethyl, each of which is optionally substituted by fluorine and/or chlorine, and Le A 30 670 1l02199846 R6 represents hydrogen, hydroxyl, amino, or represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, propenyl or propinyl, each of which is optionally substituted by fluorine, chlorine or cyano, and, if ~lopliate, with one or two compounds from a second group of herbicides 5 which contains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-bllt~n- ~te (glufosinate ammonium), ~-(hydroxymethylphosphinyl)- 1 -a-aminobutyryl- 1 -alanyl- 1 -alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) dia_in(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino- 1,3 ,S-tria_ine (atrazine), 2-chloro-4,6-bis-ethylamino- 1,3 ,5-triazine (~im~7in), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);
(d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)-1-(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or l,l'-ethylene-2,2'-bipyridinium chloride (diquat).
Le A 30 670 The following may be mentioned individually as examples of the compounds of the formula (I) to be used as components in mixtures, according to the invention:
1 -(4-chloro-3-methylsuphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-3-methylsulphonylamino-phenyl)-3 ,6-S dihydro-2,6-dioxo-3-amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-3-methylsulphonylaminophenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-3-ethylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-3-ethylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-3-ethylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-3-n-propylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimi~line, 1-(4-chloro-3-n-propylsulphonylamino-phenyl)-3, 6-dihydro-2 ,6-dioxo-3 -amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-3 -n-propylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl-1(2H)-pyrimi-lin~, 1-(4-chloro-3-i-propylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-3-i-propylsulphonylamino-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -amino-4-trifluoromethyl-1(2H)-pyrimidine, 1-(4-cyano-3-i-propylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-methylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-5-methylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-5 -methylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoro-methyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5 -ethylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2 ,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-ethylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl-1(2H)-pyrimidine~-(4-cyano-S-ethylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-n-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-5-n-propylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-amino-Le A 30 670 ~21 99 846 4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-5-n-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-chloro-5-i-propylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-chloro-5-i-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -amino-4-trifluoromethyl- 1 (2H)-pyrimidine, 1-(4-cyano-5 -i-propylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3 -methyl-4-trifluoromethyl- 1 (2H)-pyrimidine, 1 -(4-cyano-5-n-butylsulphonylamino-2-fluoro-phenyl)-3 ,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1 (2H)-pyrimidine.
The compounds of the formula (I) - or (Ia) - are described in the Patent Applications and Patent Specifications given above.
Surprisingly, it has now been found that the above-defined active compounds of the formula (I) - or (Ia) - are particularly effective in the control of weeds in the semi-selective and non-selective field, if a~ropliate in combination with the active compounds mentioned above in the second group.
The active compounds, or active compound mixtures, to be used according to the invention can be employed not only in conventional cultivation methods (row crops with suitable distances between rows) in plantation crops (for example grape vines, fruit, citrus) and on industrial terrain and rail tracks, on paths and open areas, but also for stubble tre~tment and for the ~ -tillage method. They are furthermore suitable as desiccants (haulm killing for example in potatoes) or as defoliants (for example in cotton). They are are furthermore suitable for use on fallow land. Other fields of application are nurseries, forests, grassland and in the cultivation of on ~ment~
The following may be mentioned as examples of weeds which can be controlled wellby the active compounds, or active compound combinations, according to the invention:
Le A 30 670 Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, ~nth~mi~, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesb~ni~, Ambrosia, Solanum, Cirsium, Carduus, Sonchus, Rorippa, Rotala, T intl~rni~ Lamium, Veronica, Abutilon, Emex, Sida, Datura, 5 Viola, Galeopsis, Papaver, Cellldul~a, Trifolium, P~mmçlllus, Taraxum and Mentha.
Monocotyledon weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Bra~.hi~ri~ Lolium, Bromus, Avena, Cyperus, Sorhum, A~lol~yloll, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus,Papalum, T~çh~f nnum, Sphenoclea, Dactylocenium, Agrostis, Alopecurus and Apera;
10 However, the use of the active compounds and active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
If mixtures of the compounds of the formula (I) or (Ia) with the herbicides mentioned above under (a) to (e) ("second herbicide group") are used according to the invention, 15 the weight ratios of the active compounds in the active compound combinations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight,preferably 0.01 to 100 parts by weight, particularly preferably 0.1 to 10 parts by weight, of one or two of the herbicides mentioned above under (a) to (e) are generally used per part by weight of active compound of the formula (I) or (Ia).
20 The active compounds can be converted into the cll~tom~ry formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion conc~,ll,dl~s, natural and synthetic materials impregn~te~ with active compound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active 25 compounds with e~ten~lers, that is liquid solvents and/or solid carriers, optionally with Le A 30 670 the use of snrf~ct~nt~, that is emulsifiers and/or dispersants and/or foam-formers.
If water is used as an e~t~nller~ organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkyln~rhth~lenes, chlorinated aromatics and chlorinated aliphatic 5 hydrocarbons such as chloroben7~nes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl 10 sulphoxide, and water.
Suitable solid carriers are for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina andsilicates; suitable solid carriers for granules are: for example crushed and fractionated 15 natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic m~tPri~l such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emlll.cifiers andlor foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example 20 alkylaryl polyglycol ethers, alkylsulphonates, alkyl slllph~tes, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes such as gum arabic, polyvinyl alcohol and 25 polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
Le A 30 670 It is possible to use colorants such as inorganic pigment~, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, m~ng~nese, boron, copper, cobalt, molybdenum and zinc.
S The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The novel combinations of active compound are generally deployed as ready-to-useformulations. The active compounds present in the combinations may, however, also be mixed in individual forrnulations on use, i.e. deployed as tank mixes.
10 The active compounds and active compound combinations according to the invention, as such or in their formulations, can furthermore also be used for weed control in the form of a nlix~ with other known herbicides; again, readymixes or tank mixes arepossible. A mixture with other known active compounds such as fungicides, insecticides, acarizides, nematicides, bird repellants, growth substances, plant nutrients 15 and soil conditioners are also possible. For specific purposes, it may furtherrnore be advantageous to incorporate, in the formulations, vegetation-acceptable mineral or vegetable oils (for example "Oleo Dupont 1 lE", which is commercially available) or ammonium salts such as, for example, ammonium slllph~te or ammonium thiocyanate as further additives.
20 The active compounds or active compound combinations according to the invention can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or spreading.
25 In the use experiments which have been carried out, very good properties for use in the Le A 30 670 semi-selective and non-selective field of weed control was shown by the compounds of the formula (I) or (Ia) - also in combination with the herbicides from the second group, which are mentioned above under (a) to (e), such as, for example, the isopropyl ammonium salts of N-phosphonomethyl-glycine ("Roundup").
Le A 30 670
Claims (8)
1. Semi-selective and non-selective herbicidal compositions, characterized in that they comprise an effective amount of at least one aryluracil, or an aryl-thio-uracil, of the general formula (I) (I) or of a compound of the general formula (Ia) which is isomeric to the above (Ia) where, in formulae (I) and (Ia), in each case Q1 represents oxygen or sulphur, Q2 represents oxygen or sulphur, R1 represents hydrogen or halogen, R2 represents halogen or cyano, R3 represents the group below in which A1 represents a single bond, or represents oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N- A4- where A4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, or A1 furthermore represents in each case optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulphonyl or arylsulphonyl, or A2 furthermore represents in each case optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and A3 represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy(thio)phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl, R4 represents hydrogen, halogen or optionally substituted alkyl, R5 represents hydrogen, halogen or optionally substituted alkyl, and R6 represents hydrogen, hydroxyl, amino, or in each case optionally substituted alkyl, alkoxy, alkenyl or alkinyl.
2. Semi-selective and non-selective herbicidal compositions, characterized in that they comprise an effective amount of at least one aryluracil or an aryl-thio-uracil of the general formula (I) (I) or of a compound of the general formula (Ia) which is isomeric to the above (Ia) where, in formulae (I) and (Ia), in each case Q1 represents oxygen or sulphur, Q2 represents oxygen or sulphur, R1 represents hydrogen or halogen, R2 represents halogen or cyano, R3 represents the group below in which A1 represents a single bond, or represents oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, or A1 furthermore represents in each case optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulphonyl or arylsulphonyl, or A2 furthermore represents in each case optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, and A3 represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy(thio)phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl, R4 represents hydrogen, halogen or optionally substituted alkyl, R5 represents hydrogen, halogen or optionally substituted alkyl, and R6 represents hydrogen, hydroxyl, amino, or in each case optionally substituted alkyl, alkoxy, alkenyl or alkinyl, and additionally one or more compounds from the second group of herbicides whichcontains the classes of compounds (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-butanoate (glufosinate ammonium), .gamma.-(hydroxymethylphosphinyl)-1-.alpha.-aminobutyryl-1-alanyl-1-alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo- 1 H-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) diazin(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino- 1,3,5-triazine(atrazine), 2-chloro-4,6-bis-ethylamino-1,3,5-triazine (simazin), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);
(d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)-1-(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or 1,1'-ethylene-2,2'-bipyridinium chloride (diquat).
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-butanoate (glufosinate ammonium), .gamma.-(hydroxymethylphosphinyl)-1-.alpha.-aminobutyryl-1-alanyl-1-alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo- 1 H-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) diazin(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino- 1,3,5-triazine(atrazine), 2-chloro-4,6-bis-ethylamino-1,3,5-triazine (simazin), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);
(d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)-1-(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or 1,1'-ethylene-2,2'-bipyridinium chloride (diquat).
3. Semi-selective and non-selective herbicidal compositions, characterized in that they comprise an effective amount of at least one compound of the formula (I) or (Ia) according to Claim 1 in which Q1 represents oxygen or sulphur, Q2 represents oxygen or sulphur, R1 represents hydrogen, fluorine, chlorine or bromine, R represents fluorine, chlorine, bromine, iodine or cyano, R3 represents the group below in which A1 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, or A1 furthermore represents C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene each of which is optionally substituted by fluorine, chlorine or bromine, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, or A2 furthermore represents C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene each of which is optionally substituted by fluorine, chlorine or bromine, A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen or C1-C4-alkoxy, or represents alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and each of which is optionally substituted by halogen, or represents compounds from cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate 1 to 4 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen, cyano, carboxyl, C1-C4-alkyl and/or C1-C4-alkoxy-carbonyl, or represents phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkyloxy, C1-C4-halogenoalkyloxy and/or C1-C4-alkoxy-carbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl, isoxazol-C1-C4-alkyl, thiazol-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy, furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy, R4 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, R5 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, and R6 represents hydrogen, hydroxyl, amino, or represents alkyl, alkoxy, alkenyl or alkinyl, each of which has up to 4 carbon atoms and each of which is optionally substituted by fluorine, chlorine or cyano.
4. Semi-selective and non-selective herbicidal compositions, characterized in that they comprise an effective amount of at least one compound of the formula (I) or (Ia) according to Claim 2 where Q1 represents oxygen or sulphur, Q represents oxygen or sulphur, R1 represents hydrogen, fluorine, chlorine or bromine, R represents fluorine, chlorine, bromine, iodine or cyano, R3 represents the group below in which A1 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, or A1 furthermore represents C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene each of which is optionally substituted by fluorine, chlorine or bromine, A2 represents a single bond, oxygen, sulphur, -SO-, -SO2-, -CO- or the group -N-A4- where A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, or A2 furthermore represents C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkindiyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene each of which is optionally substituted by fluorine, chlorine or bromine, A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen or C1-C4-alkoxy, or represents alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and each of which is optionally substituted by halogen, or represents compounds from cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate 1 to 4 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen, cyano, carboxyl, C1-C4-alkyl and/or C1-C4-alkoxy-carbonyl, or represents phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkyloxy, C1-C4-halogenoalkyloxy and/or C1-C4-alkoxy-carbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl, isoxazol-C1-C4-alkyl, thiazol-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy, furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy, R4 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, R5 represents hydrogen, fluorine, chlorine, bromine, or represents alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, and R6 represents hydrogen, hydroxyl, amino, or represents alkyl, alkoxy, alkenyl or alkinyl, each of which has up to 4 carbon atoms and each of which is optionally substituted by fluorine, chlorine or cyano, and additionally one or more compounds from a second group of herbicides which contains the classes of compound (a) to (e) mentioned below:
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4- D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-butanoate (glufosinate ammonium), .gamma.-(hydroxymethylphosphinyl)-1-.alpha.-aminobutyryl-1-alanyl-1-alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo- 1H-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) diazin(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino-1,3,5-triazine(atrazine),2-chloro-4,6-bis-ethylamino-1,3,5-triazine (simazin), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);
(d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)-1-(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or 1,1'-ethylene-2,2'-bipyridinium chloride (diquat).
(a) carboxylic acids such as, for example, 2,4-dichloro-phenoxyacetic acid (2,4- D), 4-amino-3,5,6-trichloro-pyridine-2-yl-oxy-acetic acid (triclopyr), ammonium 2-amino-4-(hydroxymethylphosphinyl)-butanoate (glufosinate ammonium), .gamma.-(hydroxymethylphosphinyl)-1-.alpha.-aminobutyryl-1-alanyl-1-alanine (bialaphos), N-phosphonomethyl-glycine (glyphosate) and its isopropylammonium salt and trimethylsulphonium salt, or 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo- 1H-imidazol-2-yl)-pyridine-3-carboxylic acid (imazapyr) and its isopropylammonium salt;
(b) diphenyl ethers such as, for example, 2-chloro-4-trifluoromethyl-phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen);
(c) diazin(on)es, or triazin(on)es, such as, for example, 2-chloro-4-ethylamino-6-i-propyl-amino-1,3,5-triazine(atrazine),2-chloro-4,6-bis-ethylamino-1,3,5-triazine (simazin), 5-bromo-3-s-butyl-6-methyl-uracil (bromacil) or 4-amino-6-t-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);
(d) ureas such as, for example, 3-(3,4-dichloro-phenyl)-1,1-dimethyl-urea (diuron) or 3-(4,6-dimethyl-pyrimidin-2-yl)-1-(2-methoxycarbonyl-phenylsulphonyl)-urea (sulfometuron-methyl);
(e) pyridine derivatives such as, for example, 1,1'-dimethyl-4,4'-bipyridinium chloride (paraquat) or 1,1'-ethylene-2,2'-bipyridinium chloride (diquat).
5. Semi-selective and non-selective herbicidal compositions according to Claim 2, where, in the active compound combination, the weight ratio of aryluracil, or aryl-thiouracil, of the formula (I) or of the compound of the formula (Ia) whichis isomeric thereto to an active compound from a second group of herbicides of the classes of compounds (a) to (e) which are mentioned in Claim 2 is between:
1:0.001 and 1:1000.
1:0.001 and 1:1000.
6. A method for semi-selective and non-selective weed control, characterized in that an active compound according to Claims 1 or 3, or an active compound combination according to Claims 2 or 4, is allowed to act on weeds and/or their environment.
7. Use of active compounds according to Claims 1 or 3, or of active compound combinations according to Claims 2 or 4, for semi-selective and non-selective weed control.
8. Process for the preparation of semi-selective and non-selective herbicidal compositions, characterized in that active compounds according to Claims 1 or 3, or active compound combinations according to Claims 2 or 4, are mixed wit extenders and/or surfactants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4432888A DE4432888A1 (en) | 1994-09-15 | 1994-09-15 | Use of aryluracils in the semi and non-selective area of weed control |
| DEP4432888.5 | 1994-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2199846A1 true CA2199846A1 (en) | 1996-03-21 |
Family
ID=6528309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002199846A Abandoned CA2199846A1 (en) | 1994-09-15 | 1995-09-04 | Use of aryluracils in semi-selective and non-selective weed control |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0781093A1 (en) |
| JP (1) | JPH10505603A (en) |
| KR (1) | KR970705924A (en) |
| CN (1) | CN1157552A (en) |
| AU (1) | AU3521395A (en) |
| BR (1) | BR9508929A (en) |
| CA (1) | CA2199846A1 (en) |
| DE (1) | DE4432888A1 (en) |
| HU (1) | HUT77013A (en) |
| MX (1) | MX9701953A (en) |
| WO (1) | WO1996008151A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6100218A (en) * | 1996-02-16 | 2000-08-08 | Basf Aktiengesellschaft | Substituted 2-phenylpyridines |
| US6576592B1 (en) | 1999-06-07 | 2003-06-10 | Sumitomo Chemical Company, Limited | Herbicide composition |
| US6734139B1 (en) | 1999-12-03 | 2004-05-11 | Bayer Aktiengesellschaft | N-aryl-uracile-based herbicides |
| AU780137B2 (en) * | 1999-08-03 | 2005-03-03 | Bayer Cropscience Ag | Combinations consisting of herbicides and safeners |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA971253B (en) * | 1996-02-16 | 1998-08-14 | Basf Ag | Substituted aromatic phosphonic acid derivatives |
| CN1255042A (en) | 1997-03-14 | 2000-05-31 | Isk美国有限公司 | Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them |
| DE19815820A1 (en) * | 1998-04-08 | 1999-10-14 | Hoechst Schering Agrevo Gmbh | Synergistic herbicidal agents based on leaf herbicides containing phosphorus, imidazolinones and growth herbicides |
| US6121201A (en) | 1998-09-11 | 2000-09-19 | Ishihara Sangyo Kaisha, Ltd. | Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them |
| IL167956A (en) | 2000-02-04 | 2009-02-11 | Sumitomo Chemical Co | Isocyanate compound |
| CZ304308B6 (en) | 2000-05-04 | 2014-02-26 | Basf Aktiengesellschaft | Uracil substituted phenylsulfamoyl carboxamides, process of their preparation and herbicidal composition containing them |
| US6617282B2 (en) | 2001-06-26 | 2003-09-09 | Ishihara Sangyo Kaisha, Ltd. | Processes for preparing 3-phenyl-2,4(1H, 3H)-pyrimidinediones |
| US6613718B2 (en) | 2001-10-01 | 2003-09-02 | Ishihara Sangyo Kaisha, Ltd. | Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them |
| JP4699358B2 (en) | 2003-04-08 | 2011-06-08 | ビーエーエスエフ ソシエタス・ヨーロピア | Benzenesulfonamide derivatives as herbicides or drying and / or defoliating compounds |
| WO2014012360A1 (en) | 2012-07-18 | 2014-01-23 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
| ES2663806T3 (en) | 2013-12-19 | 2018-04-17 | unshine Lake Pharma Co., Ltd. | Heterocyclic nitrogen derivatives and their application in the treatment of tissue fibrosis |
| BR112020012345A2 (en) | 2017-12-19 | 2020-11-24 | Syngenta Crop Protection Ag | substituted thiophenyl uracils, their salts and their uses as herbicidal agents |
| WO2019121543A1 (en) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
| WO2019121547A1 (en) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
| EP4003975A1 (en) | 2019-07-22 | 2022-06-01 | Bayer Aktiengesellschaft | Substituted n-phenyl-n-aminouarcils and salts thereof and use thereof as herbicidal agents |
| CN114401956A (en) | 2019-07-22 | 2022-04-26 | 拜耳公司 | Substituted N-phenyluracils, their salts and their use as herbicides |
| US20220411381A1 (en) | 2019-10-01 | 2022-12-29 | Bayer Aktiengesellschaft | Pyrimidinedione derivatives |
| MX2023002206A (en) | 2020-08-24 | 2023-03-06 | Bayer Ag | Substituted n-phenyluracils and salts thereof, and use thereof as herbicidal active substances. |
| EP4230620A1 (en) | 2022-02-22 | 2023-08-23 | Bayer Aktiengesellschaft | Substituted n-amino-n-benzoic acid uracils, their salts and use of said compounds as herbicidal agents |
| EP4230621A1 (en) | 2022-02-22 | 2023-08-23 | Bayer AG | Substituted n-benzoic acid uracils, their salts and use of said compounds as herbicidal agents |
| WO2023161172A1 (en) | 2022-02-22 | 2023-08-31 | Bayer Aktiengesellschaft | Substituted n-benzoic acid uracils and salts thereof, and use thereof as herbicidal active substances |
| WO2024078906A1 (en) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituted n-phenyluracils and salts thereof, and use thereof as herbicidal active substances |
| WO2024104952A1 (en) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituted cyclopropyloxyphenyluracils and salts thereof, and use thereof as herbicidal active substances |
| WO2024104956A1 (en) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituted cycloalkylsulfanylphenyluracils and their salts, and their use as herbicidal active substances |
| WO2024104954A1 (en) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituted cycloalkyloxyphenyluracils and salts thereof, and use thereof as herbicidal active substances |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084084A (en) * | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| US5169430A (en) * | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
| JPH05125057A (en) * | 1991-11-01 | 1993-05-21 | Sumitomo Chem Co Ltd | 1-phenyl-4-trifluoromethyluracil derivative and herbicide containing the same as active ingredient |
| US5602077A (en) * | 1992-01-15 | 1997-02-11 | E. I. Du Pont De Nemours And Company | Pyrimidine compounds as herbicides |
| JPH06271409A (en) * | 1993-03-18 | 1994-09-27 | Nissan Chem Ind Ltd | Herbicide composition |
| JPH0753313A (en) * | 1993-08-13 | 1995-02-28 | Nissan Chem Ind Ltd | Herbicidal composition |
| DE4412079A1 (en) * | 1993-08-18 | 1995-02-23 | Bayer Ag | N-Cyanoaryl-nitrogen-heterocycles |
-
1994
- 1994-09-15 DE DE4432888A patent/DE4432888A1/en not_active Withdrawn
-
1995
- 1995-09-04 BR BR9508929A patent/BR9508929A/en not_active Application Discontinuation
- 1995-09-04 CN CN95195061A patent/CN1157552A/en active Pending
- 1995-09-04 CA CA002199846A patent/CA2199846A1/en not_active Abandoned
- 1995-09-04 HU HU9701964A patent/HUT77013A/en unknown
- 1995-09-04 EP EP95931983A patent/EP0781093A1/en not_active Withdrawn
- 1995-09-04 WO PCT/EP1995/003472 patent/WO1996008151A1/en not_active Application Discontinuation
- 1995-09-04 JP JP8509868A patent/JPH10505603A/en active Pending
- 1995-09-04 AU AU35213/95A patent/AU3521395A/en not_active Abandoned
- 1995-09-04 MX MX9701953A patent/MX9701953A/en unknown
-
1997
- 1997-03-12 KR KR19977001634A patent/KR970705924A/ko unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6100218A (en) * | 1996-02-16 | 2000-08-08 | Basf Aktiengesellschaft | Substituted 2-phenylpyridines |
| US6576592B1 (en) | 1999-06-07 | 2003-06-10 | Sumitomo Chemical Company, Limited | Herbicide composition |
| AU780137B2 (en) * | 1999-08-03 | 2005-03-03 | Bayer Cropscience Ag | Combinations consisting of herbicides and safeners |
| US6734139B1 (en) | 1999-12-03 | 2004-05-11 | Bayer Aktiengesellschaft | N-aryl-uracile-based herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10505603A (en) | 1998-06-02 |
| KR970705924A (en) | 1997-11-03 |
| HUT77013A (en) | 1998-03-02 |
| CN1157552A (en) | 1997-08-20 |
| EP0781093A1 (en) | 1997-07-02 |
| AU3521395A (en) | 1996-03-29 |
| WO1996008151A1 (en) | 1996-03-21 |
| BR9508929A (en) | 1998-01-06 |
| DE4432888A1 (en) | 1996-03-21 |
| MX9701953A (en) | 1997-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2199846A1 (en) | Use of aryluracils in semi-selective and non-selective weed control | |
| US5990044A (en) | Selective herbicides based on aryl uracils | |
| MXPA97001953A (en) | Employment of ariluracils in the semi-selective and non-selective field of the fight against bad hier | |
| US6331507B1 (en) | Substituted aromatic thiocarboxylic acid amides and their use as herbicides | |
| CA2460915C (en) | Herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(ethi)ones | |
| JPH08208412A (en) | Herbicide based on aryl uracil for being used in cultivationof rice plant | |
| MXPA97002552A (en) | Selective herbicides based decarbamoiltriazolinonas and deheteroariloxiacetami | |
| JP2003510258A (en) | Selective herbicides based on N-aryl-triazoline (thio) ones | |
| WO1997005117A1 (en) | Substituted 1-phenyluracil derivatives, their preparation and their use as herbicides | |
| AU705366B2 (en) | Substituted aryl sulphonyl amino(thio)carbonyl-triazolin(thi)ones as herbicides | |
| US6159903A (en) | Substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones as herbicides | |
| AU718868B2 (en) | Substituted p-trifluoromethylphenyluracils | |
| WO1998002422A1 (en) | Substituted aromatic carbonyl compounds and their derivatives | |
| DE4424787A1 (en) | Substituted arylimino heterocycles | |
| DE19500439A1 (en) | Substituted aromatic thiocarboxylic acid amides | |
| US6187716B1 (en) | Heterocyclyluracil | |
| CA2216064C (en) | Selective herbicides based on metribuzin and substituted imidazo[1,2-a]pyridin-3-yl-sulfonyl compounds | |
| US6444616B1 (en) | Substituted p-trifluoromethylphenyluracils | |
| US6451738B1 (en) | Substituted thienyl(Amino)-sulphonyl(thio)ureas as herbicides | |
| US5030272A (en) | Selective herbicidal agents containing metamitron in combination with certain triazolinones | |
| CA2202617C (en) | Selective herbicides based on carbamoyltriazolinones and heteroaryloxyacetamides | |
| EP0784431B1 (en) | Synergistic active substance herbicide combinations with 1-(2,6-dichloro-4-difluoromethyl-phenyl)-5-(2-chloropropionamido)-4-nitropyrazol | |
| US4925483A (en) | Triazinone synergistic compositions | |
| MXPA99000363A (en) | Substitute carbonil-aromatic compounds and susderiva |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |